(S)-[2-(benzyl-tert-butoxycarbonyl-amino)-3-phenyl-propylideneamino]-acetic acid methyl ester | 863408-73-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-[2-(benzyl-tert-butoxycarbonyl-amino)-3-phenyl-propylideneamino]-acetic acid methyl ester
• 英文别名: methyl 2-[[(2S)-2-[benzyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-phenylpropylidene]amino]acetate
• CAS: 863408-73-5
• 化学式: C₂₄H₃₀N₂O₄
• 分子量: 410.513
• InChiKey: APHJLWPTEYQIQJ-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-[2-(benzyl-tert-butoxycarbonyl-amino)-3-phenyl-propylideneamino]-acetic acid methyl ester 在 silver(I) acetate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  A stereodivergent cascade imine→azomethine ylide→1,3-dipolar cycloadditive approach to α-chiral pyrrolidines

  摘要：

  Stereodivergent [3+2] cycloadditions of chiral alpha-amino azoinethine ylides leading to highly functionalized pyrrolidines are reported. The marriage of substrate conformational preferences and either an inter- or intramolecular cycloaddition manifold leads to either the l (syn) or u (anti) relationship between the pyrrolidine and alpha-stereocenters. The latter result may be applicable to a new approach to the bioxalomycin family of antibiotics. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.119
• 作为产物：
  描述：

  (S)-2-(benzylidene-amino)-3-phenyl-propionic acid methyl ester 在 sodium tetrahydroborate 、 magnesium sulfate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 23.5h， 生成 (S)-[2-(benzyl-tert-butoxycarbonyl-amino)-3-phenyl-propylideneamino]-acetic acid methyl ester
  参考文献：
  名称：

  A stereodivergent cascade imine→azomethine ylide→1,3-dipolar cycloadditive approach to α-chiral pyrrolidines

  摘要：

  Stereodivergent [3+2] cycloadditions of chiral alpha-amino azoinethine ylides leading to highly functionalized pyrrolidines are reported. The marriage of substrate conformational preferences and either an inter- or intramolecular cycloaddition manifold leads to either the l (syn) or u (anti) relationship between the pyrrolidine and alpha-stereocenters. The latter result may be applicable to a new approach to the bioxalomycin family of antibiotics. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.119

文献信息

• A stereodivergent cascade imine→azomethine ylide→1,3-dipolar cycloadditive approach to α-chiral pyrrolidines
  作者：Philip Garner、H. Ümit Kaniskan

  DOI：10.1016/j.tetlet.2005.05.119

  日期：2005.8

  Stereodivergent [3+2] cycloadditions of chiral alpha-amino azoinethine ylides leading to highly functionalized pyrrolidines are reported. The marriage of substrate conformational preferences and either an inter- or intramolecular cycloaddition manifold leads to either the l (syn) or u (anti) relationship between the pyrrolidine and alpha-stereocenters. The latter result may be applicable to a new approach to the bioxalomycin family of antibiotics. (c) 2005 Elsevier Ltd. All rights reserved.